N-(tert-butoxycarbonyl)glycine → HCID 86758536, compound

HRID 989644Notes

Reaction equation

HRID 989644 reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][C:5]2[CH2:6][CH:7]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[C:8](=[O:12])[N:9]([CH3:11])[CH2:10][C:4]=2[CH:3]=1.[C:20]([NH:27][CH2:28][C:29](O)=[O:30])([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>>[C:23]([O:22][C:20]([NH:27][CH2:28][C:29]([NH:1][C:2]1[CH:19]=[CH:18][C:5]2[CH2:6][CH:7]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[C:8](=[O:12])[N:9]([CH3:11])[CH2:10][C:4]=2[CH:3]=1)=[O:30])=[O:21])([CH3:26])([CH3:25])[CH3:24]

Participants

3

Reactant 2

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 53747305HCID 53747305, compound

Product 1

HCID 86758536HCID 86758536, compoundYield 55%

Procedure

Methyl (±)-8-amino-2-methyl-3-oxo-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate was coupled with Boc-glycine according to the procedure of example 5(b). Purification by chromatography (silica gel, 2%-5% CH3OH/CH2Cl2) gave the title compound as a pale yellow foam (55%): 1H NMR (CDCl3) δ8.22 (br s, 1H), 7.48 (s, 1H), 7.20 (d, J=8.3 Hz, 1H), 7.04 (d, J=8.3 Hz, 1H), 5.27 (d, J=16.6 Hz, 1H), 5.25 (br s, 1H), 3.92 (d, J=5.4 Hz, 2H), 3.82 (m, 1H), 3.80 (d, J=16.6 Hz, 1H), 3.71 (s, 3H), 3.03 (s, 3H), 2.90 (m, 3H), 2.41 (dd, J=16.8, 5.5 Hz, 1H), 1.48 (s, 9H).

Workup

  1. customPurification by chromatography (silica gel, 2%-5% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-1ba7fa9e25c749858d6aa36d6979c8e5
Source dataset
uspto-grants-2002_10
Patent number
US06458784B1

Reaction notes

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